Are some trolls clever? From IRS: You may deduct gambling losses only if you itemize deductions. What Is a Hobby Loss?gambling commercial go to your box HOW GAMBLING AFFECTS THE ECONOMY What Is a Gambling Loss? Some jurisdictions allow taxpayers to write off losses incurred through gambling. As a result, these countries typically allow gamblers to deduct their losses in order to reduce tax liability. The process for claiming a gambling loss can be complex. No. You can offset gambling losses if you have gambling income but the gambling losses can't be more than the gambling income. I see nothing strange about that. August 23rd, at PM permalink. Hello, It is my general understanding that you can only write off your gambling losses only against your wins and that you have to itemize your winnings The courts have ruled that if a person keeps a detalied log it shall be valid evidence for the gambler.